Kelowna, British Columbia, Cananda

Ainsley Wynter

Ainsley (they/she), is an educator and organizer originally from Toronto, now living in British Columbia. Ainsley is a genderfluid lifestyle submissive, embodying a blend of one part disarming innocence and one part misleading kindness.

They are a wholehearted submissive who enjoys donning their favorite bossy skirt and heels on the right occasion. When it comes to personal favorite kinks, Ainsley can easily be found engaging in excited discussions about D/s dynamics, high protocol, needle play, CBT, and chastity devices.

Ainsley originally found their love for teaching and organizing as a long serving organizer for TNG Toronto. Over the last year, they have been serving as the volunteer coordinator for Westcoast Bound, taught at Taboo Vancouver, Working out the Kinks Kamloops, and Kinkfest in Portland. Looking ahead, Ainsley will be an Educator for Westcoast Bound 2024, along with continuing their role as Volunteer Coordinator and continuing to grow and learn from their peers around them.


Crafting an Environment of Feminized Empowerment

Imagine you place your hand on the door, slowly opening it into a party. The door opens, you struggle to keep your balance with each step you make in your heels. The metal lock clicking against your chastity cage is heard from under your short skirt with each step. You look in the mirror across the hall and see your perfect sissy self looking back.

Join Ainsley as she dives into the world of gender play aimed for all. Shining a light on creating your sissy identity and bringing it into your play we discuss common archetypes, protocols, outfits and toys. Let's talk about how to bring it all together while empowering yourself and growing your confidence. Grab your favourite heels, cutest outfit, and most of all don’t forget your questions as we look at developing your inner sissy and the world of gender play through sissification.

Please note: This class will NOT cover any form of gender based play as humiliation.

The Art and Allure of Urethral Sounding

Join Ainsley in the enigmatic allure of the dungeon, where a captivating world unfolds. Participants will tune their senses to the whispers of curiosity as they embark on an intimate exploration of urethral sounding. They will watch as a shimmering metal rod ventures into unseen territories, delicately navigating the fine line between ecstasy and intensity.

In this class, participants will dive deeply into both the artistry and psychology of sounding. They'll discuss the various tools used, emphasizing safety as the guiding principle. They will learn to approach this skill with the utmost respect, infused with an atmosphere of fun and laughter, building a foundation of trust and consent. Together, they will explore the intertwined realms of power, trust, and vulnerability, unveiling new dimensions of pleasure and connection. Participants are encouraged to engage fully, ask questions, and learn the skills to navigate multiple metal rods in a wonderfully new way.

Please note, the class will focus exclusively on external genitalia and will include a demonstration. Participants should get ready for an enlightening session filled with sound fun.